Numford
Name reaction

Wurtz reaction

Two molecules of an alkyl halide react with sodium in dry ether to give a higher alkane with double the carbon atoms of the alkyl group.

Class 11, Chapter 9 Hydrocarbons

  1. Br
    BromoethaneCH₃CH₂BrHaloalkane
  2. Step 1

    Na, dry ether

    Wurtz reaction
    i

    Wurtz reaction doubles the alkyl group; only symmetrical alkanes are made cleanly.

    ButaneCH₃CH₂CH₂CH₃Alkane

Reagents: Na, dry ether

Mechanism

How it works

  1. Sodium reacts with the alkyl halide to form an alkyl sodium (or radicals).
  2. The alkyl group attacks a second molecule of halide.
  3. The new C-C bond forms and NaX is lost.
Used to prepare

What it makes

Symmetrical alkanes with an even number of carbons.

Limitations

Where it fails

A mixture of two different halides gives three alkanes, so it is used for symmetrical alkanes only. Methane cannot be made.

Which chapter

Class 11, Chapter 9 Hydrocarbons

Questions

Wurtz reaction: quick answers

Why must dry ether be used?

Sodium reacts with water, and moisture would destroy the alkyl sodium.

Can the Wurtz reaction make methane?

No, it joins two alkyl groups, so the smallest product is ethane.

What does a mixture of CH3Cl and C2H5Cl give?

A mixture of ethane, propane and butane.

Plan an organic conversion